Sharp Dressed Man
by elanurel
Summary: There was a reason why Dean Winchester didn’t play dress up unless it was for a job and her name was Betty Lou Perkins. Adult Content.  Teen!Chesters.  COMPLETE


**Sharp Dressed Man**

Sam could make cracks about chicks digging a man in uniform until he was blue in the face but it wouldn't change a thing. There was a reason why Dean Winchester didn't play dress up unless it was for a job and her name was Betty Lou Perkins. Even her _sister_ thought she was the Antichrist with pom-poms.

This is an interesting piece, where the past and present collide. It is a companion piece to both Backdoor Man and Iambic Pentameter and Other Methods of Elizabethan Torture.

* * *

**Disclaimer:** The Winchester boys aren't mine but I'd make Dean wear his boots all the time if they were.

**Rating**: M (Language, Sex)

**Pairings**: Dean/OFCs

Spoilers/Warnings: No spoilers. Underage sexual situations - hey, Dean's 17.

**Beta: **The lovely **embroiderama** once again let me spam her with IM and reassured me that, despite some of the crappier stuff going on in my life, my porn fu was strong. Everything that rocks in this piece is because of her. The mistakes? Those are all me.

* * *

"Why the hell would I even _want_ to do that?"

"This coming from the man who's always trying to get me to wear _high-heeled_ shoes in public."

"That's different. I've got my reason for not dressing up unless it's for a job."

His voice was muffled against his t-shirt, black cotton replaced by gray eyes and a smile. She leaned forward, licking a stripe up one of the silvered scars on his chest, before tilting backwards to rest on her hands – long legs straddling his thighs. Her face was flushed, red hair falling against cream-colored wool as he untied her belt, and she was spread out in front of him wearing nothing but a goddamn granny sweater; half-slipping off her shoulders as he brought his mouth down, her body arching up into his lips.

"What's her name?"

It came out half-gasp, half-question – strawberry-scented sweat in his mouth, mixed with sloe gin and musk and the rasp of wool against his arms as he flicked with his tongue. Tendons stretched when her head fell backwards with an 'ah' and she cradled his neck with one hand.

"Why do you think it's a chick?"

Another half-gasp, half question – one hand sliding past the elastic of his boxers, her thumb working in counterpoint to her fingers against more sweat and musk and a slickness that throbbed. She rocked forward, softly scratching underneath his hair as a smile brushed against his temple.

"Because every single one of your stories ends with a girl."

* * *

Her name was Betty Lou Perkins – and she was stacked.

It wasn't hard to notice, that first time she walked by his locker wearing a tight little white t-shirt, cotton spreading across her chest like she could burst out of the low neckline with a just a laugh. The flip of blonde curls over her shoulder when she'd passed him gave off the same message as the sway of her hips underneath her plaid skirt, the same answer he heard in every girl's laugh.

She kept right on walking when Dean grinned at her, hair swirling back around her shoulders, and the guy standing at the locker next to Dean just chuckled. _She's out of your league, man._ The geek had a chemistry book and something that looked like a comic book tucked under his arm, and he pushed his glasses up his nose. _Betty Lou's the captain of the cheerleading squad. She only likes jocks._

Dad had been chasing after a monster that looked like a loose-limbed puppet with claws and teeth to match, the Impala roaring into Pensacola a month after the Fall semester had started. Every new town meant a new school. It was one of the rules, part of Dad's plan – even if they only stayed for a month or two.

Schools meant discipline.

There was enough action in the area to keep Dad busy for awhile but evil sons of bitches didn't work on a time table. They rolled into town too late for any of the Fall team try-outs. Some of the clubs were still taking on new members but Dean would be caught dead before someone caught him playing chess with a bunch of nerds or doing that drama stuff after school. It was bad enough that Sam thought his middle school science club was _cool_.

Dad never let them slack – no matter how long they were staying in one place – and physical training was another part of their routine. It was just as easy to jog around the track on the game field in front of the cheerleading squad as it was to do it around the block a couple of times. He'd have to take Sam out again after dinner but that was a small sacrifice. Betty Lou wouldn't be able to keep her eyes off of him once Dean reached full speed.

He _ran_ like a jock.

Especially after that hunt with Dad in New Mexico went south. For such little suckers, chupacabras were fucking fast.

Kids were milling all over the field by the time Dean was sitting on the bleachers, tying off his sneakers in front of the cheerleading squad. The football team was doing their tire thing and a bunch of girls sat on a nearby retaining wall, watching them and giggling when one of the players waved at them. The cheerleaders were already warmed up, shaking pom-poms and doing whatever else cheerleaders did before they really started practicing.

Dean stretched out against the lower tier of the bleachers, keeping as keen an eye on Betty Lou Perkins as half of the cheerleading squad was keeping on him – not to mention some of the chicks who were sitting with the drama club. They were sitting higher up on the bleachers, messing up the lines in whatever play they were rehearsing. Most of them just laughed but one chick stared at him over the top of her paperback, eyes more serious than the rest.

It was time to set the plan into motion.

He kept his stride loose and easy, breathing in time to the rhythm of his heartbeat, during his first lap. He lengthened his pace, barely a burn in his muscles while he circled the track.

Betty Lou didn't look at him until his third lap past the squad, her cheeks pink from all that pyramid building and arm flapping, and she returned his grin on the fourth lap. By the fifth lap, Dean picked up speed and ran like those chupacabras were following him.

It had been easier than knocking pop cans off a fence with a BB gun.

The next day, she stopped at his locker long enough to grab his wrist with one hand and started walking, pulling him behind her with another look over her shoulder. Dean grinned down at the kid who was pulling out his chemistry book and slammed his locker shut. They didn't stop until they reached the janitor's closet. Dean pushed her up against the wall, their teeth clicking while her hands wound behind his neck.

Her tongue flickered in his mouth and she moaned when Dean's hands slid underneath her shirt – bright pink and just as tight as the one she wore the day before – but she was pushing him backwards at the same time. _Show me_, she said. _Show me how much you really want me, new boy_.

And Betty Lou Perkins staked her claim right then and there in the janitor's closet, one finger running along the length of his fly – making him hard enough to say 'yes' when that finger slid back up to the button at his waist.

* * *

"You want to know something stupid? I used to want to be a cheerleader."

She was leaning backwards again, elbows resting on the bed. Their eyes met when he spread her thighs wider, scars peeking through the lattice of his fingers. They were lighter on the inside of her thighs, where the fire hadn't gotten so far in, and he dipped his mouth down to lick the salty skin where her hip curled into her pelvis.

"Why would you want that? That cheerleader was the Antichrist with pom-poms. And you call yourself a girl genius."

"You're the only one who calls me that."

"A girl genius who keeps interrupting me."

He chuckled, tonguing the white scar that pointed right between her thighs. She was trembling, pushing herself up to meet him with a soft sigh. He brushed against her once and she bolted against the mattress.

"If I'm so smart, you should give me some – "

He started flicking his tongue.

Suddenly her hands were behind his head, pulling him deeper; bones like liquid while she undulated against his mouth. She groaned when he replaced his tongue with three fingers; sliding them gently at first, thrusting harder as her hips rocked. He rested his other hand on her abdomen, watching her back bow, and she came with a small swell.

"I'll give you some once I've got your _undivided_ attention."

Her hips rolled, pulse warm and musky. He was drowning in the taste of her, his hands covered in the scent of her; her sweater slipped down her arms when she bucked up into his face and there was slick sweat on his shoulders from the backs of her knees.

When she screamed, clutching the comforter with both hands and throbbing against his lips, he nearly came himself – as hard as he had been the day some blonde-haired cheerleader ran her finger down the zipper of his jeans.

"You going to be quiet now so I can finish my story?"

* * *

Dad always went where the job took him and he wasn't very picky about the schools they ended up in so long as they got decent grades and kept up with their training when he was somewhere else working on a job. He'd even give them assignments, which boiled down to long afternoons spent with Sam doing research in the local library, and Dad would quiz them afterwards to see what they learned.

If it had been up to Dean, he'd be getting Betty Lou off in some hidden nook behind the stacks instead of watching Sam eat his fruit roll-up and flip through a book on witchcraft during the Middle Ages but the gig didn't work that way.

Besides, the football game was only two days away.

And there were ways to deal with frustration, even if Sam made that _face_ every time Dean came out of the bathroom. It wouldn't be too long before the kid was doing it himself.

Dean figured that he was lucky – the football team was called the Pensacola Fighting Privateers and not something lame like the Pensacola Fighting Pandas – until he asked Sam what a privateer looked like. Sammy just rolled his eyes and left the table. Five minutes later, Sam was opening up a history book and showing him some dude with puffy pants, a frilly shirt and tights.

At least the conquistador on the next page got to wear _armor_, even if it was just some flimsy-looking breastplate that probably wouldn't stop a bullet.

Not that it mattered. The temporary mascot gig meant that he'd be wearing an oversized Pensacola Fighting Privateer head; no one but Betty Lou Perkins would even know that the dude in the puffy pants was Dean Winchester – and once they snuck back into her house, even the frills on the collar would have been worth every promise she wrapped up in just one kiss.

Getting his hands on the damn thing was the real problem.

The dweeb who usually danced around in the mascot outfit during games was out of town – and Betty Lou had _no_ idea where the costume was kept when it wasn't being worn. Neither did the rest of the cheerleaders, half of the pep band, his entire Algebra II class or random kids who passed by his locker in the hall. Dean's imminent failure hadn't kept Betty Lou from taunting him on breaks between classes in the janitor's closet, pushed up against the wall while he kissed her hard; giving him a pout and a small whisper when they broke for air.

_Don't you want me, new boy?_

He would just have to improvise.

And no one could improvise like a Winchester, whether it was melting down Hot Wheels to make bullets in a pinch or souping up mac and cheese with half a can of spam and a handful of frozen peas. He dragged Sammy back to the library for the history book but there was no way in hell Dean could jury rig something from Dad's "working clothes." Even with some of the stranger stuff, there was nothing that remotely matched the goddamn privateer's costume.

Well, maybe he'd be able to manage the _sword_. And Sam's old mask from last year's Halloween costume would hide Dean's face to the point of not being recognizable.

It would have been a _hell_ of a lot easier if the football team was called the Pensacola Fighting Priests. At least Dad had a collar he could have used for that.

There was nothing left to do but move on to Plan B – taking what he needed from the old costume room behind the stage in the auditorium. It wasn't even stealing, technically. Dean wasn't going to be keeping a pair of puffy pants around any longer than he needed to get into Betty Lou's white panties. He'd just sneak back into school after claiming his prize and no one would even know the clothes were gone. It's not like anyone would have kept a list of all the crap stuck in the room.

Plan B wouldn't get set into motion until Friday.

He waited for the game to start. With everyone out in the stands, no one would be wandering the halls watching the new boy carry a crumpled paper bag with him into the auditorium – or be there to see to him hitch himself up onto the stage.

The door to the costume room was locked but it didn't stand a chance against Dean Winchester and a paper clip. No one would ever accuse him of being a boy scout but Dad was always telling them to be prepared. When he flicked the light switch, there was one old bulb swinging on a fixture in the middle of the room – shadows reflecting off of rows and rows of costumes on old clothing racks. There were tables in the back covered with bolts of fabric and one sewing machine.

The old time clothes were in the back of the third row, on a rack topped with a yellowing sign that had "Romeo and Juliet" written on it in a flowery script. He flipped through outfits, finding one in black that would match Sammy's Zorro mask; at least he'd be keeping the dork factor as low as he could but, when he slipped on the puffy pants, they fell right back down. The green pair wasn't much better and the blue outfit was a woman's dress.

The only male costume that fit was _purple_, covered with a trim that sparkled – even under the light of one lone bulb.

By the time Dean figured out how to attach the sleeves to the vest thing, the band was playing outside. Half time had already started. He didn't have much time. He'd promised Betty Lou one shoulder ride at half time and then he was home free and sliding right into her pants. He left his clothes kicked in a pile and pulled on the mask, pushing his feet into his boots and slamming the door behind him.

His feet pounded concrete until he decided to take a shortcut, running underneath the bleachers and exiting out from the other side just in time to see Betty Lou Perkins' throwing her arms around some dude in a football player's outfit, tangling tongues under the bright spotlights from the stands.

It was the fucking quarterback, an asshole named Todd who liked to tip trays when kids stumbled past his table in the cafeteria.

And Todd sure as hell wasn't wearing purple _tights_.

There was a girl standing off to the side of the bleachers, wearing a flowery dress and watching the same scene with both arms wrapped across her stomach. Her hair whirled as she turned to run but she stopped right in her tracks when she saw Dean in his sparkly privateer get-up, eyes going round and shiny. She opened her mouth like she was going to say something and then pushed past him, knocking into his arm as she ran – hard-soled shoes against the concrete and a whisper that sounded like 'Todd' in her wake.

Dean wasn't going to let Betty Lou Perkins get off that easy.

He hid in the shadows and watched the second half, grimacing every time she flipped blonde curls whenever the quarterback ran past the cheerleading squad. Even Dean had to admit that the fucking quarterback was _good_. Seconds after throwing the winning touchdown, the crowd converged on the field and his team threw him up onto their shoulders. Betty Lou was beaming up at Todd before she was swept up in the surge.

It didn't take long for the jubilant crowd to pass – none of them noticing the figure crouched in the shadows underneath the bleachers, despite the sparkles from his goddamn clothes.

There was supposed to be a dance going on in the gym and someone might catch him in the hallway but Dean had a mission. He found them in a deserted corner of the parking lot, underneath a broken light post; Betty Lou's moan poured out of a cracked-open window and the car actually squeaked when it rocked back and forth.

The damn bastard might have gotten the cheerleader but his car sucked _ass_.

* * *

"The chick was screwing him in a freaking _Camry_."

"Even _I_ would choose the back of your crap car over a Camry."

"I'm never going to finish this story if you keep interrupting me."

She was curled onto her side, head balanced on one folded arm. A ghost of a smile crossed her face, her other hand drawing slow circles on his right hip and scratching just enough to make him quiver. She left one trail of kisses up his jaw line before she shifted and sprawled across him, the metallic clink of quarters dropping next to his ear right before the bed started humming.

"And you just insulted my baby. Don't even think that's going to soften me up."

"I hope not."

Her body slid back down his, straddling him as she moved, and her hair fell onto his neck as she bent forward – sighing into his mouth. His nails grazed her back underneath the coarse wool, from her shoulders down to her ass, and she arched into it like a cat before settling onto her knees. The sweater skimmed her hips, the cuffs pooling around her hands splayed open on each of his thighs. He was already springing up to brush against her lips, fingers digging into the muscles of his legs as she touched it with the tip of her tongue.

Dean grabbed tight onto her hair, tugging hard. He wanted to taste her, to feel her squirm on top of him as the vibrations worked their way into the wetness and he was soaking in strawberries and sloe gin all over again – but she held her ground, fingers playing him right to the edge. His body buckled along with the buzzing through his belly every time her head bobbed and she flicked his pulse in counterpoint to his groaning.

His hands were still in her hair when she backed off, hot breath eddying across glistening skin.

"Jesus…"

"I… I improvised."

He shivered when she leaned down to kiss his hip, letting go of her hair. She was back on her side – arm flung across his waist with another kiss to his shoulder and her face was a flush against him.

"Are you _blushing_?"

Her entire body was hot to the touch, her cheeks turning an even brighter red when he let out a low chuckle, and she whispered against his neck.

"Are you going to finish your story now?"

"Only if you promise to keep improvising like that when you interrupt me again."

* * *

The whole thing was a total bust and the only good thing about the freaking dance was the fact that the gym was on the opposite side of the school – so there wasn't much of a chance that anyone would see him skulking back to the auditorium.

A thin line of light greeted him from underneath the door when Dean finally made it back to the costume room. He didn't think anything of it – he'd run like hell to reach the game before half time was over – until he'd pushed the door in and heard the soft catch of a sob, muffled by the rows of clothes; a girl was standing near one of the tables in the back, her head bent like one of those angel statues in a cemetery.

Dean tried to back out the door before she saw him but her head whipped up and she glared at him, her voice a whip. _You shouldn't be here._

He was about to tell her to join the club despite the goddamn tear tracks on her face but then he recognized her flowery dress – and there was something even more familiar about the way her blonde hair curled around her shoulders, like she should have been staring at him with a smile instead of looking like bombs were getting ready to explode in her eyes.

Whatever the chick's problem was, all Dean wanted to do was change his clothes and try to salvage the rest of the night – but she didn't look like she was going to just let him go and he was damned if he was going to wait around and get yelled at by a girl. The clunk of her boots on the hard floor matched his as they met in the middle of the room, her eyes hurt all over again, and she said the one thing that snapped his mouth shut faster than a command from Dad.

_My little sister is the Antichrist with pom-poms._

The resemblance was impossible to miss up close and personal, not when the girl was staring up at him with the same curves underneath the floral print – doing her sister one better with nipples pushing through the thin fabric and a catch in her throat when she reached up and pulled off the mask. _You're not even wearing it right_, she whispered. _The sleeves are inside out. _Her fingers were already working the knots on one sleeve where it tied to the vest thing, brow furrowed with concentration. He'd learned how to tie knots from a pro. But none of that could keep the glimmer from shimmering in her eyes and the final piece to the whole thing fell into place when music from the gym filtered into the room.

He leaned forward, hands on her hips, and her entire body stiffened. The hair on her neck prickled underneath his smile.

_Let's get even._

She pulled back like a shot, her eyes narrowing, and Dean knew he was seconds away from getting clocked by a chick. He braced his feet, because the only thing the night needed to end on the crappiest note ever was for him to get knocked flat on his ass by a girl with a grudge.

He must have done something right because the girl threw her arms around his neck and slammed her mouth into his.

Betty Lou Perkins had nothing on her sister when it came to kissing. The damn girl was pulling him backwards towards the fabric covered tables, back arching as she hitched up onto something that felt like velvet. And she wasn't wearing a bra, moaning as he tongued a nipple through the fabric – hands scrabbling to get the goddamn vest off of him while he flipped up her flowery dress and saw the panda-covered panties underneath.

The panties were down around her ankles and he dipped his mouth down, a moan and a shove against his lips were all that it took for him to begin looking for the goddamn button on his pants. She found it herself, pulling them down while he pushed between his knees. Her hands got caught in the waistband of the freaking tights, bursting against the seam.

_Fuck it_, he managed and began rubbing his crotch against hers, going faster and faster as she kicked off her panties and braced her boots behind the backs of his knees.

* * *

"So I ended up coming in a pair of tights."

"Not your finest…moment."

She bit her lower lip while she straddled him, pushing down with a groan. He strained against her as she rocked, a sticky sweet friction that shot one long pulse through her – and she trembled along the length of him, tilting her head up so that he could capture her mouth with his, hair falling behind her like red rain while she gripped onto the headboard and bucked against him with the aftertaste of sloe gin.

He reached up and grabbed the collar of the sweater, coarse and uneven in his hands, and ripped it off – using the leverage from her arms suddenly flying off the headboard to push her onto her back. He pinned her to the bed with a hand on each knee, sliding between her thighs. Her eyes widened, nails sliding down his arms, and she bucked once against him.

"You ever try explaining to your dad why you're washing a pair of purple tights in the motel room sink?"

One thrust for each syllable, hard staccato beats as her pulse fluttered against his; it made him crazy, watching the slick slip and slide as she curled into him – legs tightening around his waist and fingers digging hard into his sweat-soaked back as she held on, head falling backwards with another 'ah' that throbbed through him.

She met each push with a lift of her hips, the edges blurred as he moved hard and slow and like a goddamn jackhammer when she stuttered a dare of 'harder' right into his ear – shattered in the wet and the deep and the taste of strawberry sweat everywhere his lips touched, drowning in broken pieces whenever she moaned. Or gasped. Or called out his name and looked right up into his eyes. There was scratching and screaming – her nails down his back and his hands holding tight into her hips and everything started pouring into her until she was overflowing.

All he could manage, between the catch in his chest and her tongue making a stripe up his neck, were three words.

"I'll…do it."

She hitched herself up, plastering his mouth with hers, and he pulled back just long enough to breathe.

"But I'm only doing it once. And if Sam _finds_ the black nail polish and the eyeliner, I'm saying that they're yours."

"Do I look like the kind of girl who wears black nail polish?"

"Do I look like the kind of yahoo who goes commando in a _kilt_?"

She smiled against his mouth.

"You can leave your boots on."

* * *

A/N:

Obviously, I used the song "Sharp Dressed Man" by ZZ Top for the title of this story.

As usual, I did my best to tone down the adult content. If more work is needed in that regard, please let me know.

This is set in one of my 'verses but it's such a stand-alone piece that 'verse knowledge was completely unnecessary. Seriously, it was Dorky!Dean with a side of serious smut. Those of you who have read the 'verse, however, should have no problem recognizing the girl. She's dorky, too…

More specifically, the "modern" parts of the story are a direct sequel to "Backdoor Man" whereas the tragic tale of Dean in high school is based on an incident he divulges in "Iambic Pentameter and Other Methods of Elizabethan Torture." The past has finally collided with the present in the _Strange Angels_ 'verse.

Yes, I paraphrased "You Can Leave Your Hat On" for this. Bwa ha ha…

And, for the record… The Elizabethan thing was for everyone who asked me to write the story based on "Iambic Pentameter and Other Forms of Elizabethan Torture." Think about this for a moment: Jensen's thighs in tights. The black nail polish was for embroiderama. The eyeliner and kilt was for everyone with a Priestly fetish. The boots? They were totally for me. (Hey, a girl's got to keep her spirits up when she's got bronchitis.)


End file.
